The Miltons Vs The Winchesters
by StarSlashedHeroine
Summary: This is a rewrite for my high school AU of Supernatural
1. The Invites

**Author's Notes**- Ok so I re-read Milton's vs Winchesters and decided to do a rewrite and hopefully it will turn out better with the grammar and all that jazz. Same basic concept thought I just switched up a few things. I am in such a writing mood so between this, my Sterek fanfic, and my Original work, I hope to keep my juices flowing. Destial and Sabriel main ships. High School A/U

I don't own Supernatural this is strictly for fun. Parts of me seriously wish I did though.

**Chapter One- The Invites**

It was a fairly warm afternoon in late October, so the short skirts fluttering by Dean as he lay outside on the bleachers wasn't a shocking or unpleasant surprise. He sits up, yawning, stretching his arms over his head exposing some on his abs to the crowd.

"Think they'll lift their skirts if you lift your shirt Winchester." Dean narrows his eyes looking to the left seeing his friend Jo hop up onto the bleachers. He puts his arms down as she comes over sitting next to him. She looks out over the football field with him as it beings filling up with students from Lawrence High.

"What's happening?" Dean scratches the back of his neck as he watches a couple more people walk by.

"Who man where have you been? Dean my brother from another mother it it's the Wednesday before All hallows eve. Time for our gods and goddesses to pass out the invited to the hedonistic heaven that is the Milton's." Ash says as he plops down behind Dean and Jo flipping his mullet off his shoulder.

"Already?" Dean's voice gruff from nonuse as he reaches into his backpack and pulls out a drink sipping on it. "I didn't think it was so close to that time."

"Time moving too fast for you Deano?" Jo questions taking his drink for herself. Dean just shakes his head and sees his brother coming out from the cafeteria with his girlfriend Jess carrying and extra tray of food.

"Thanks Sammy." Dean takes the tray when his brother gets close enough and Sam narrows his eyes at him but sits on the bottom bleacher with Jess by his side.

The crowd begins to quiet down as the two Milton's still remaining at Lawrence High headed out to the field, since all the others had graduated. There was six of them total but only two under the legal age to being doing half the shit that goes on at their parties.

The Milton's were Lawrence's answer to the Kennedy's or Baldwin's or any pop group put together over the last twenty some odd years. They are rich, athletic, intelligent and extremely good looking, everything that Dean and his group weren't. Some of Dean's group had a couple of those qualities but not all of them.

The oldest two, Michael and Raphael, ran the family business since their father had retired and moved to some island with his new twenty something bride. But this also meant that they wouldn't stop being rich anytime soon. Michael was a shred business man and Raphael his loyal puppy, doing whatever Michael said.

The first of the middle children caused the family great shame and Michael has been trying to rebuild a positive reputation around the town again. Lucifer Nicholas "Nic" Milton was currently in a maximum security prison for the murder of Karen Singer, Marley Singer and attempted murder of Bobby Singer, who were people all very close to the Winchesters. Marley had been like and older sister to Dean and Same, who Nic decided to kill after apparently being rejected too many times, her mother just got in the way. That was over ten years ago.

The youngest three Milton's were also the closest in age, a year or barely a year separating each of them. First was Gabriel who graduated last year but was still floating around the time, claiming he was taking some time off before going to college. He was smarter than any one gave him credit for cause is loud mouth and obsession with sweets are what sticks in people's minds the most.

Then there was the two positioning themselves in the middle of the field surrounded by their followers. Anna, there only girl in the group, was the Queen of the high school with her bitches Meg and Ruby following her everywhere. They were all seniors like Dean and Dean has had to fend off Meg more than one time. And Castiel who stood looking off to the side. Dean didn't know much about Castiel other than the fact that he was in Sam's grade and too smart to still be in high school. Dean watches the tall blonde behind Castiel lean forward, and Jo grumbles something about how creepy she thinks Balthazar is. Dean snickers.

Castiel moves away from the group and over to the side of the road as a white Porsche pulls up to the curve. Dean watches as Lilith, Ruby's other sister gets out and hands the hot off the presses invites to Castiel before kissing his cheek, whispering something then getting back in her car and leaving. Castiel walks back over to Anna and Anna brings handing the invites out.

Dean and his group never got invited and he was ok with it being that way. The only one who was allowed to go was Jo. But that was only because her mother worked as the Milton's cook during the day. She had practically grown up with them but thankfully she had better since to be friends with them at school, or at least that is what Dean thought most the time.

The group of five watch the envelopes get passed out as they eat their lunches. The Milton's are about done as the Outsiders were too busy talking to themselves to realize that Castiel had moved in front of them. He clears his throat, all of them stop talking and look at him. Dean's eyebrows nearly leave his forehead in shock.

"Hear Sam…Jess…" Castiel's voice made Dean question his sexuality. The deep tones went straight threw his veins down to his cock. Sam and Jess timidly take the invites to the party. Jess is gleaming with excitement. "Jo…Anna insists…Ashley."

"Yo dude…its Ash." He takes the invite, Anna only invited Ash because he is Jo's oldest friend and she really wanted Jo to show up at the last Halloween party should would be throwing.

Dean's eyes trace over all the invites in his friend's hands and his lips purses slightly. He looks up feeling Castiel's intense stare upon him. Dean shifts a little as Castiel tilts his head to the side slightly and there was no way that Dean thought it was cute. Nope. The rest of Dean's group finally realized he didn't get and invite. Sam was about to give his back to Castiel when Jess caught his hand glaring down at him daring him to continue.

Sam looks up at Dean apologetically and Dean just shrugs at him sort of letting him know it would be ok. Castiel lifts a brow and smirks. He turns on his heel as sees some random person who got and invite walking by. Castiel reaches out and pulls it out of his hand, the guy goes to get lippy but sees Castiel narrowing his eyes at him. He frowns walking off to mope. Castiel turns around and looks up handing the invite to Dean.

"Anna is going to kill me, but this only seems fair." Dean takes it and looks over at Jo who laughs and then he looks back at Castiel. "You better show up…all over you." Castiel stops looking at Dean's lips and looks at the rest of the group before walking off.

Jo busts out laughing "Looks like the littlest Milton has his eyes on you." Dean jerks his head to his left and glares at her just causing her to laugh more.


	2. Halloween

**Author's Notes-** Ok so I am really bad about attempting to type up new chapters while trying to decide if my bed is correctly pronouncing my name. So like all my works all my mistakes are mine. Also my smut is sadly a little rusty hope its ok.

I don't own Supernatural this is strictly for fun. Parts of me seriously wish I did though.

**Chapter Two-** Halloween.

Dean was in the kitchen when Jo and Ash came over with the costumes for the Milton's party. He was digging through the spice cabinet and pulling things out as he shuffled things around. Jo comes in and leans on the counter in her sexy Laura Croft outfit, toy water guns on her thighs and all as Ash ran Dean's costume up to his room.

"What in Sam hell are you doing Dean? Gonna cook them a pie before going over? If so 'fraid these ain't enough time for that." Jo says as she plays with the end of her braid.

Dean pulls down the last thing he was looking for and turns around glaring at her. "Like I would waste a perfectly good pie on the Milton's. They are not worthy of pie."

"They what are you doing?" She moves over and looks at the salt and hot pepper powder on the counter.

"You think I am going to give up my one chance to mess with the Milton's. I may never get invited back into that place. Hell knows I can't get past that damn head of security they have. So I am going to make the most of this and enjoy my night." Then he proceeds to pull a bag of itching powder out of his pocket. "Bobby was willin to give my fireworks to set off in the place, but I decided to keep the pranks simple and avoid jail time."

"Seriously Dean…?" Jo shakes her head as he gathers up his stuff. "Ash took your costume upstairs go put it on or we're going to be late."

"What did I get?" Dean asks looking over her outfit. Jo quirks a brow and shakes her head pushing him towards the steps.

Dean gets up to his room and sees the bag on his bed and opens it. "You got to be kidding me?!"

Ash comes down the steps snickering. Sam follows him down in an ER version of Dr. Sexy, scrubs face mask and cowboy boots. Jess is right behind him in a slutty nurse outfit. Sam pulls his mask down and looks at Ash and Jo. "What did you all get him?"

"Oh it's going to be good, Jo had to sweet talk the store clerk into giving us a discount. Or else Dean woulda been going in his birthday suit." Ash states.

"Jo can sweet talk?" Sam asks in disbelief and Jo smacks him upside the head. "Shut it Winchester Jr."

Twenty minutes later and Jo is glaring at the clock on the wall. "Dean hurry up…"

"I hate you both you know this right." He states as he comes down the steps in a very authentic looking Batman costume. Gripping and hugging all his muscles, only letting his lush lips and green hazel eyes shine through. "How am I supposed to sit in this thing?"

"Well you can just lay down in the back of the Impala and I'll drive Dean." Sam smirks.

"Nice try Sammy but you're not touching my baby. What the hell Ash? What are you supposed to be?" He looks at Ash who looks just like himself, no costume on at all.

"I'm Billy Ray Cyrus buddy. He rocked the mullet. Knew the virtue of a true hair style." Jo laughs and Dean just shakes his head no.

"It's not fair I have to wear this thing and you get to go like that. You need a more humiliating costume." Dean glares at him.

"Too late for that we gotta go." Jo grabs Dean's hand and hauls him out the front door.

-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-

Sam had lost Dean as soon as he got into the foyer of the Milton estate, mumbling something about his utility belt. Sam had just shook his head. He stood there awkwardly looking around at the grand stair care and the two massive rooms to either side. People were everywhere and a lot not even from their school.

He sighs as Jess drags him off into the living room. She is smiling and waving at people as they walk along. Finally they stop on the far side of the room which gave them a good view of everyone else in the room. Jess looks around all excited bouncing on her heels a bit to the music. She finally looks up at Sam.

"I'm going to go see if I can find some snacks." Sam nods at her as she walks off.

Sam turns around turning his attention the mantle that his back had been pressed firmly against and stares looking over the pictures. He makes his way from the mantle to a book shelf slowly reading the titles. He gets to the door way connecting to the kitchen and sees Jess. He smiles and then sees her give her flirty face and gentle place her hand against Brady's arm.

Brady had been his best friend in middle school but they really didn't talk anymore. Sam couldn't help but feel a pain in his heart seeing Jess flirting with Brady, who was clearly flirting back.

"Domestic problems Doc?" Sam jerks out of his thoughts and looks down to his side to see Gabriel Milton by his side.

Sam's breath caught as his eyes zoomed in on the lollipop rolling seductively between his lips staining them red. Gabriel's golden eyes lock with Sam's as his tongue licks out over the lollipop. Sam gasps slightly and Gabriel smirks holding up a beer.

"House rules, everyone gets a drink Doc. And from what I've seen you haven't had one."

"You've been watching me?" Sam feels his cheeks heat up at the thought of Gabriel watching him. Sam had come to the conclusion his freshman year, the first time he saw Gabriel, to not label himself because he knew he was attracted to the man.

"Well when a tall, built, firm…mmm… Doc with a nice ass shows up at your door you tend to pay attention. So was I right Doc…? Your nurse making her rounds?" Sam looks back over at Jess who is looking at him slightly embarrassed. Gabriel leans up pressing the drink into Sam's hand. He puts his lips next to Sam's ear after removing the lollipop. Sam could smell the cherry candy on his breath. "If I was your nurse I would want to go rounds with you in only those boots."

Jess comes over clearing her throat and Gabriel moves away with a smile on his lips popping the sucker back into his mouth and pulling it back out with an obscene pop. Sam knows his face is red and couldn't be more thankful for the mask Ash supplied him with. Gabriel Milton just hit on him, that's if Gabriel even knew who he was, but either way Gabe thought he was hot. Try as Jess might it took her a good ten minutes to get Sam out of his own head.

-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-\m/\m/-

Dean was wondering around the upstairs after successfully adding massive amounts of salt to various liquor bottles and applying hot pepper power to the keg pump and a couple doors. He sighs and notices there isn't actually many people up here. He shrugs his shoulders and finds the bathroom. He pushes the door closed behind him but it doesn't latch.

He pulls the itching powder out of the utility pouch and begins to put it on the toilet paper.

"Now that doesn't seem like a very heroic thing for batman to be doing."

Dean freezes dropping the pack of itching powder on the floor. He turns around slowly and is greeted by a heavy bosom covered only by a skimpy French maids outfit. His eyes slowly drift up to Lilith's face and he shallows hard. She hums to herself as she walks around him slowly.

"Now what am I going to do with a renegade cape crusader?" She taps her red lips as she stops in front of Dean. "I could call Uriel or I could not tell anyone. There for letting you live. But for me to do that you would have to agree to cheer up my Sassy little one."

"Huh?"

"Either come with me and entertain my friend or I am going to get Uriel up here and let him give you a new asshole to shit threw. Was that clear enough for ya batman?" Dean can see Lilith is getting irritated.

"I guess I can entertain (?) Your friend." Dean wasn't exactly sure what that meant but Lilith smiles and grabs a wash cloth and wets it wiping any itching powder off Dean that might have gotten on him before taking his hands and leading him down the hall.

They get to the last door in the hallway and Lilith pushes the door open.

"Sassy I brought you a present." No response "I'll leave it here for you." Lilith grabs Dean's shoulder and whispers into the ear hole. "Don't even think about leaving once I close this door, I know Uriel is itching to beat a young punk like you into a pulp so behave."

She shoves him forward and turns the lock on the knob and pulls it shut behind her as she leaves. Dean stands still letting his eyes adjust to the room that was only lit by the moonlight coming in there the window. Dean sees a figure sit up on the bed pushing itself to the end. Flick. The bedside table light clicks on and Dean is blinking his eyes readjusting again.

He finally focuses looking over at the bed and to his surprise he sees Castiel Milton sitting on the bed. His dark brown almost black hair sticking out all over the place, he full lips pursed as his head is slightly tilted taking in Dean. He is dressed up like Aladdin, sheer fabric vest and harem pants. His toned chest exposed to Dean who was finding it hard to not look the boy over.

Castiel slides off the bed and moves over to Dean. He repeats the appraisal Lilith gave him, walking around him. Castiel trails one of his hands over Dean's ass threw the suit. Dean sucks in his lower lip as he feels the fingers firmly trailing his ass. Castiel stops right in front of him and those killer blue eyes lock on his.

Dean releases his lip, he has no clue what is happening to him, but Castiel has him questioning everything he knows with the lusty look in his eyes and slightly parted lips. Dean flexes his fingers but keeps his hands by his side. The next thing Dean knows is that there are plush lips against his own. Slotted just right for Castiel not to hurt himself on the mask.

Castiel's tongue licks against the seam of Dean's mouth and presses against it until Dean finally opens up. Castiel slides his hands up Dean's arms feeling his muscles through the suit before hooking them around the back of his neck. Castiel's tongue works Dean's tongue into playing back eventually Dean startles himself by moaning when Castiel sucks on his tongue.

He moves his lips from Dean's ear and kisses along the exposed bits of jaw. Castiel then moves back pulling Dean with him. Dean follows blindly not coming to any form of his senses until Castiel pushes him back onto the bed and moves up straddling his lap. Dean's eyes open wide snapping him as of his sex haze.

"Look Cas I'm not gay."

"Cas?" Castiel's voice did things to his cock that made him momentarily happen to be wearing the stupid suit. "So you know me? Interesting."

"I…no…I don't really know you." Dean could answer honestly because he had never really had any interaction with Castiel. "I just don't know what you're expecting from me."

Castiel gives him a wicked smirk before leaning back into Dean pressing their lips together again, he trails along again ending at the ear hole for the suit. "I want your cock." Castiel grinds down into Dean's lap and Dean groans. "I want to taste it, feel it…swallow it down till I wish I had a gag reflex." Castiel pulls back putting his hands on Dean's chest and looks at him with innocence in his blue eyes. "Please…" Castiel pouts and Dean is a goner.

Dean licks his lips and nods his head yes. Castiel smiles and slides down his body working the bottom half of the costume off dragging it down Dean's legs. He gets it down past his knees the pulls don't Dean's boxers with a gasp.

"You certainly won't disappoint Batman…" Castiel ducks his head down out of Dean's vision. Dean can feel Castiel's hot breath ghosting over the head of his cock before he tentatively licks it from root to tip. Dean tosses head back as Castiel's nimble fingers wrap around his shaft to hold him up as he gets even harder. He twirls his tongue around the tip getting his tongue along the crown and into the slit.

Dean's hips jerk up and Castiel removes his hand and smiles as Dean's cock stands at attention. "Cas…" Dean drags a raspy breath as he leans up on his elbows. He immediately falls back down as Castiel sucks in the head of his cock. The warm wet heat surround him Dean couldn't think of any other blow job he had gotten starting off this well.

Castiel sucks in his cheeks and moves his head down Dean's cock he gets about midway before he released his cheeks and loosens his throat bobbing up and down a few times before he nestles his nose in the hair at the base of Dean's penis. Dean tries to control his urge to come as much as he can because it would be embarrassing to come this soon.

Dean finally manages to prop himself up on his elbows as he watches Castiel go to town. Suck and groaning and licking along his dick. Dean's hands are gripping the sheets tightly. Castiel locks his eyes with Dean after sliding off the bed and down in between Dean's legs. He only his ex blew him like this they might still be together.

Castiel pops off Dean's cock and wraps two slender fingers around the base as Dean started to show signs of coming. Dean growls at him and Castiel smirks.

"How do you know me batman?" His voice even rougher due to the abuse he was putting his throat threw.

"I'm…uh…not saying."

"Do you want to come?" Dean nods yes. "Then give me something and I'll let you come down the back of my throat."

Dean rolls his head back and groans as Castiel uses his other hand to start stroking up and down on his saliva covered cock. Dean growls again while biting on his lower lip.

"Fine…fine…we go to the same school and I have seen you around that's how I know who you are now put your mouth back on my dick."

"Hmm…" Castiel thinks as Dean tells him they go to the same school, then smirks as Dean goes onto demanding action. "Mmm anyone ever tell you, you have a voice for giving orders…its hot."

Castiel smirks before quickly taking Dean's cock back into his mouth and going all the way down removing his fingers. Dean almost automatically shoots down Castiel's throat. Castiel swallows it all as he slowly slides back up. He licks his lips as his Adam's apple bobs. He leans down and licks over Dean's cock before moving back. Dean can see the bulge coming out of Castiel's pants and almost feels the urge to return the favor but Castiel is off heading to his en suite bathroom before words can leave his mouth.

"Be gone by the time I get back." Castiel says and he goes into the bathroom.

Dean sat there dumbfounded for a while before standing up slowly and pulling his boxers and pants back up and walking out of the room in a slight daze.

"What a fucked up night!" Dean mumbles to himself as he moves through the hall.


End file.
